Positional distribution of DHA in triacylglycerols: natural sources, synthetic routes, and nutritional properties.

Docosahexaenoic acid (DHA, 22:6 n-3) is a long-chain polyunsaturated fatty acid (PUFA) present in high quantities in the mammalian brain and is a precursor of several metabolites. Clinical trials have demonstrated the benefits of dietary DHA in infants and adults. Triacylglycerols (TAGs) are the most abundant components of many natural oils, and in specific oils (e.g., fish, algal oils, etc.), they represent the main molecular form of dietary DHA. The positional distribution of DHA in the TAG glycerol backbone (sn-2 vs. sn-1/3) varied among different sources. Recent studies have shown that in human breast milk, DHA is mainly esterified at the sn-2 position (∼50% DHA of the total DHA), thus attracting research interest regarding the nutritional properties of sn-2 DHA. In this review, we summarize the different sources of TAG in natural oils with high amounts of DHA, including fish, algae, and marine mammal oils, with a focus on their positional distribution. Methods for analyzing the distribution of fatty acids in TAG of high-PUFA oils are discussed, and the lipase-catalyzed synthetic routes of specific triacylglycerols with sn-2 DHA are summarized. Furthermore, we discuss the recent research progress on the nutritional properties of DHA associated with its positional distribution on TAGs.